Asymmetric Synthesis and Function Development of Silicon-Stereogenic Novel pi-Conjugated Compounds

2019 Fiscal Year Final Research Report

• Project/Area Number: 16H04145
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Osaka University
• Principal Investigator: SHINTANI Ryo 大阪大学, 基礎工学研究科, 教授 (50372561)
• Project Period (FY): 2016-04-01 – 2019-03-31
• Keywords: 不斉ケイ素中心 / π共役化合物 / 触媒的不斉合成

Outline of Final Research Achievements

Optically active compounds are widely used in various fields including medicines, pesticides, and organic materials, but asymmetric synthesis of silicon-stereogenic organosilanes had not been well investigated. In this research, we focused on the development of catalytic asymmetric synthesis of silicon-stereogenic silicon-bridged pi-conjugated compounds and examination of the properties of resulting compounds in the hope of expression of chiroptical properties. As a result, we could achieve the synthesis of various silicon-bridged pi-conjugated compounds such as dibenzosilole derivatives that were difficult to synthesize using existing methods. We could also succeed in obtaining those compounds with high enantioselectivity in many cases. In addition, we could acquire important information on the mechanisms of the reactions we developed as well as optical properties of the compounds we synthesized.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究は、これまであまり研究がなされてこなかった不斉ケイ素中心を持つ化合物の不斉合成のなかでも、分子の機能開拓を念頭に置いてケイ素架橋π共役化合物を主なターゲットとした反応開発および物性評価に関するものであり、学術的新規性は非常に高いと考えられる。研究の性質上、その成果がすぐさま社会に還元されるわけではないが、本研究によって、新たな分子変換反応の開発を通じて様々な不斉ケイ素中心を持つ新しい有機ケイ素化合物の不斉合成が可能になるとともに、得られた化合物の物性評価においても一定の成果を挙げることができ、有機合成化学ばかりでなく、有機金属化学や材料化学など関連諸分野への貢献は大きいと言える。